Selecting Planning Software and Tools

The personal-finance software landscape has been remade in the last three years. Mint shut down on March 23, 2024¹ after Intuit folded what was left of the experience into Credit Karma. Personal Capital became Empower Personal Dashboard in February 2023² under its new owner, and NewRetirement rebranded as Boldin in September 2024³ to broaden beyond retirement-only planning. Any guide to selecting tools is, by definition, a snapshot — what follows is the April 2026 cut, with the categories that actually matter and prices verified against the live product pages.

Categories (Match the Tool to the Decision)

The category dictates everything else: budgeting tools answer “where did the money go?”, planning tools answer “will the money last?”, and analytics tools answer “is the portfolio doing what I think it’s doing?” Most users need one tool per category, not a single tool that does all three poorly.

Budgeting and Cash-Flow Tools

These pull transactions from your banks, categorize them, and let you set monthly limits or zero-based budgets. Strong on tracking and discipline; weak (or absent) on retirement projections, Roth conversions, and tax modeling.

The Mint replacement question. Monarch Money was founded by Mint’s first product manager and absorbed a large share of its user base after the shutdown.⁴ If you’re rebuilding a budgeting workflow from scratch and want the closest analog to old Mint with active development, Monarch is the default starting point. YNAB if you want the discipline of a zero-based method. Simplifi if you only want cash-flow and don’t care about budgeting envelopes.

Retirement Planning and Monte Carlo Tools

This is where DIY users do real work: Roth conversion ladders, Social Security claiming optimization, tax-aware withdrawal sequencing, sequence-of-returns risk. These platforms charge for serious modeling, not for transaction tagging.

Be careful conflating products. Two errors I’ve seen in older guides: (1) listing Mint as a current option — it’s been gone for two years; (2) treating “Personal Capital,” “Empower Personal Dashboard,” and “Empower Personal Wealth” as different products — they’re the same product across rebrands. Same trap with NewRetirement and Boldin: same platform, new name.

Investment Analytics Tools

Specialized tools for portfolio analysis and performance attribution. Useful when account aggregation alone doesn’t surface what you need.

Advisor-Tier Software (For Context)

If you engage a fee-only planner, they’ll likely use one of these. Pricing isn’t publicly listed on most; planners build the cost into their AUM or flat-fee schedule.

• eMoney Advisor — comprehensive cash-flow planning with deep estate modeling; owned by Fidelity. https://emoneyadvisor.com/
• MoneyGuidePro / MoneyGuideElite — goals-based planning, the largest market share among advisors. https://www.moneyguidepro.com/
• RightCapital — modern UI, strong tax-strategy and student-loan modules. https://www.rightcapital.com/
• Holistiplan — tax-focused; ingests Form 1040 and surfaces planning opportunities (Roth windows, IRMAA brackets, capital-gains harvesting). Premium tier starts ~$1,499/yr. https://www.holistiplan.com/pricing/

Critical Features (How to Evaluate)

Account Aggregation Quality

Aggregation pulls balances and transactions automatically; reliability varies by data provider (Plaid, MX, Yodlee, Akoya, or proprietary). Broken connections produce stale projections.

• Number of supported institutions — major platforms support 15,000+
• Update frequency — daily is standard; intra-day uncommon outside professional tiers
• Connection durability — if a connection breaks weekly, the tool is unusable for serious planning
• Manual asset support — needed for real estate, private equity, fine art, crypto self-custody

Monte Carlo Methodology

Monte Carlo simulations roll thousands of return paths to estimate the probability that a plan survives. Quality varies sharply.

• Number of trials — 1,000 is the floor; 10,000+ for narrow confidence intervals
• Return assumptions — historical mean/variance versus capital-market expectations (forward-looking)
• Correlation modeling — do asset classes co-move realistically under stress?
• Sequence risk weighting — early-retirement bear markets are heavier than late-career ones
• Fee handling — are investment costs deducted from returns?

Reading the success-rate output:

A 100% success rate isn’t an aspiration; it usually means the plan is leaving money on the table.

Tax Projection and Optimization

Where DIY-grade tools start to differentiate from advisor-grade software. Look for:

• Multi-year Roth conversion analysis — solves for optimal annual amount, not just “should I convert”
• Tax-loss harvesting flags
• Asset-location optimization — placing the right asset class in the right account type
• Social Security claiming-age modeling with lifetime-tax (not just lifetime-benefit) framing
• RMD projections with future-bracket forecasts

Reporting and Visualization

You’ll look at the dashboard far more than the assumption page. It needs to:

• Show net worth over time, with components
• Track goals against spending and savings rates
• Display return distributions (not single-point estimates)
• Visualize cash-flow waterfalls and tax-bracket utilization

Cost by User Type

DIY Individual

You can omit the analytics layer if you hold simple index funds — Boldin and Empower’s free dashboard cover most of what you’d actually use it for.

High-Net-Worth Household ($1M+ investable)

Concentrated stock, equity comp, multi-state taxation, estate complexity — DIY tools start to fall short.

Or skip the DIY stack and engage a fee-only advisor at $3,000–$10,000/yr. The breakeven on advisor cost is usually one well-timed Roth conversion ladder, one concentrated-stock diversification plan, or one Social Security claim sequencing decision.

Worked Example: David and Maria, age 52

Profile:

• Combined income $285,000; investable assets $1,340,000 across 401(k), IRA, Roth IRA, and taxable
• Primary residence valued $650,000 with $180,000 mortgage
• Goal: retire at 62, target $120,000/yr spending in today’s dollars
• Complexity: David holds $200,000 of company stock (concentrated); Maria has a pension paying $35,000/yr starting at 65

Three configurations evaluated:

Option A — Boldin PlannerPlus ($144/yr)

Strengths: Roth conversion year-by-year recommendations; Social Security optimizer; Medicare/IRMAA-aware healthcare modeling; pension integration with COLA support.

Limitations: Concentrated-stock tax modeling is light; collaboration with an outside advisor is awkward.

Output: 84% plan success at $120K spending. Recommends $50K/yr Roth conversions ages 62–65. Both spouses delay Social Security to 70.

Option B — ProjectionLab Premium ($129/yr)

Strengths: Side-by-side scenario comparison; cleanest cash-flow visuals; FIRE-aware sequence-risk modeling.

Limitations: Account aggregation less robust; tax projections shallower; pension support requires manual workarounds.

Output: 82% plan success at $120K spending. Scenario test: retiring at 60 drops success to 71%, with clear visualization of the spending-flexibility cost.

Option C — Fee-only advisor with RightCapital access ($4,500/yr ≈ 0.34% on $1.34M)

Strengths: 10,000-run Monte Carlo with full distribution tail; tax-bracket visualization across a 30-year horizon; concentrated-stock diversification with explicit tax modeling; estate-planning integration; live human interpretation.

Limitations: Higher headline cost; depends on advisor quality.

Output: 86% plan success at $120K spending. Identifies a $45,000 tax bill if the company-stock position is liquidated in a single year. Five-year diversification schedule saves ~$12,000. Pension COLA modeled accurately.

Recommendation: Given the concentrated stock and pension complexity, the advisor’s tax-aware diversification plan saves enough across a few years to cover the fee multiple times over. For a similar household without concentrated stock or pension complexity, Boldin PlannerPlus is the right answer at 1/30th the cost.

Implementation

Initial Setup

1. Inventory accounts and credentials. Use a password manager.
2. Establish aggregation links. Verify balances against statements after first sync.
3. Add manual data. Real estate, pension projections, expected inheritances, equity comp vesting schedules.
4. Set assumptions. Inflation 2.5–3%, return expectations from current capital-market assumptions, spending pattern by year.
5. Run a baseline. Document the current trajectory before changing anything.
6. Sanity-check. Compare a key output (e.g., projected portfolio at age 65) against a back-of-envelope compounding calc.

Ongoing Maintenance

Selection Checklist

Needs assessment

• Define primary objective (budgeting, retirement, tax)
• Inventory accounts and complexity (RSUs, pensions, real estate, private holdings)
• Assess DIY-vs-guided preference honestly
• Set an annual tools budget

Feature evaluation

• Verify aggregation supports your specific banks/brokers
• Confirm Monte Carlo trial count and methodology
• Test tax projections against a scenario you already understand
• Check mobile and web parity
• Review data-export options (CSV/PDF) for portability

Trial

• Use the free trial — don’t trust marketing copy
• Input real account data (not toy data)
• Compare outputs against your own spreadsheet on one critical question
• Test customer support response time

Implementation

• Secure all credentials in a password manager
• Complete account linking and verify accuracy
• Add manual data (real estate values, pension specifics, SS estimates from ssa.gov)
• Set realistic assumptions for your time horizon

Ongoing

• Monitor aggregation health monthly
• Update assumptions when capital-market expectations shift materially
• Export data annually for backup
• Reassess tool fit every 2–3 years; the category moves fast